Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0372)
Drug Name
Colchicine
Synonyms
Gloriosine; N-Deacetyl-N-formyl Colchicine; N-Deacetyl-N-formylcolchicine; N-Formyl-Deacetylcolchicine; N-Formyl-N-deacetylcolchicine; Formyldescaetylcolchicine, N-; N-Formyldeacetylcolchicine; N-Formyldesacetylcolchicine; U02803H7OJ; AC1L2N2A; BRN 2824080; CHEMBL85710; COLCHICINE, N-DEACETYL-N-FORMYL-; Formamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)-; N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]formamide; NSC 403142; NSC403142; UNII-U02803H7OJ
Indication Uncontrolled gout [ICD11: FA25] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 385.4 Topological Polar Surface Area 83.1
Heavy Atom Count 28 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
23890
PubChem SID
473586 ; 8141688 ; 8167432 ; 26756917 ; 29291001 ; 49955736 ; 57331490 ; 77548941 ; 84981402 ; 103291345 ; 104359407 ; 124892459 ; 134987857 ; 135626447 ; 162259585 ; 175607868 ; 187051827 ; 212342872 ; 230031014 ; 241144181 ; 243170643 ; 252370558
ChEBI ID
ChEBI:27882
CAS Number
64-86-8
TTD Drug ID
D09DHY
Formula
C21H23NO6
Canonical SMILES
COC1=CC=C2C(=CC1=O)C(CCC3=CC(=C(C(=C32)OC)OC)OC)NC=O
InChI
1S/C21H23NO6/c1-25-17-8-6-13-14(10-16(17)24)15(22-11-23)7-5-12-9-18(26-2)20(27-3)21(28-4)19(12)13/h6,8-11,15H,5,7H2,1-4H3,(H,22,23)/t15-/m0/s1
InChIKey
HDSXDWASQCHADG-HNNXBMFYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
2-O-demethylcolchicine DM003714
23757
Oxidation - Demethylation 1 [6]
3-O-desmethylchochicine DM003715
299664
Oxidation - Demethylation 1 [6]
Colchicine metabolite M1 DM003713 N. A. Unclear 1 [7]
Colchicine metabolite M6 DM003709 N. A. Unclear 1 [7]
Colchicine metabolite M7 DM003706 N. A. Unclear 1 [7]
Colchicine metabolite M8 DM003712
234105
Unclear 1 [7]
Colchicine metabolite M2 DM003707 N. A. Unclear 2 [7]
Colchicine metabolite M3 DM003708 N. A. Unclear 2 [7]
Colchicine metabolite M4 DM003710 N. A. Unclear 2 [7]
Colchicine metabolite M5 DM003711 N. A. Unclear 2 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012811 Colchicine Colchicine metabolite M7 Unclear Unclear [7]
MR012814 Colchicine Colchicine metabolite M6 Unclear Unclear [7]
MR012817 Colchicine Colchicine metabolite M8 Unclear Unclear [7]
MR012818 Colchicine Colchicine metabolite M1 Unclear Unclear [7]
MR012819 Colchicine 2-O-demethylcolchicine Oxidation - Demethylation CYP3A4 [6]
MR012820 Colchicine 3-O-desmethylchochicine Oxidation - Demethylation CYP3A4 [6]
MR012815 Colchicine metabolite M6 Colchicine metabolite M4 Unclear Unclear [7]
MR012816 Colchicine metabolite M6 Colchicine metabolite M5 Unclear Unclear [7]
MR012812 Colchicine metabolite M7 Colchicine metabolite M2 Unclear Unclear [7]
MR012813 Colchicine metabolite M7 Colchicine metabolite M3 Unclear Unclear [7]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1558 Streptomyces griseus Not Available Not Available [4] , [5]
⏷ Show the Full List of 10  DME(s)
References
1 Colchicine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Colchicine down-regulates cytochrome P450 2B6, 2C8, 2C9, and 3A4 in human hepatocytes by affecting their glucocorticoid receptor-mediated regulation. Mol Pharmacol. 2003 Jul;64(1):160-9.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Microbial catalyzed regio-selective demethylation of colchicine by Streptomyces griseus ATCC 13273. Appl Biochem Biotechnol. 2017 Nov;183(3):1026-1034.
5 Resistance of alkaline phosphatase of human serum to the protease of Streptomyces griseus. Biochim Biophys Acta. 1968 Jun 4;159(2):405-7.
6 Colchicine-antimicrobial drug interactions: what pharmacists need to know in treating gout
7 Identification of novel metabolites of colchicine in rat bile facilitated by enhanced online radiometric detection

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